Trifluoroacetic acid → HCID 86687578, compound

HRID 1473521Notes

Reaction equation

HRID 1473521 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])=[CH:9][CH:8]=[C:7]([S:20]([N:23](CC1C=CC(OC)=CC=1)[C:24]1[S:25][CH:26]=[CH:27][N:28]=1)(=[O:22])=[O:21])[CH:6]=2.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])=[CH:9][CH:8]=[C:7]([S:20]([NH:23][C:24]1[S:25][CH:26]=[CH:27][N:28]=1)(=[O:21])=[O:22])[CH:6]=2

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86687575HCID 86687575, compound

Product 1

HCID 86687578HCID 86687578, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-bromo-N-(4-methoxybenzyl)-4-(2-methoxyphenyl)-N-(thiazol-2-yl)quinoline-7-sulfonamide (from STEP 1 of EXAMPLE 324, 15 mg, 0.025 mmol) in DCM (1 mL) was treated with TFA (0.5 mL). After 30 min, the mixture was diluted with MeOH, and then concentrated in vacuo. The residue was purified by chromatography on silica gel (12-g Redi-Sep Gold column, 0-5% MeOH/DCM) to give 3-bromo-4-(2-methoxyphenyl)-N-(thiazol-2-yl)quinoline-7-sulfonamide (11.8 mg, 0.025 mmol, 99% yield) as a light-yellow solid. 1H NMR (400 MHz, DMSO-d6) δ=13.12 (br. s., 1H), 9.06 (d, J=4.4 Hz, 1H), 8.44 (d, J=1.8 Hz, 1H), 7.85 (dd, J=1.9, 8.9 Hz, 1H), 7.69 (s, 1H), 7.62-7.48 (m, 3H), 7.34-7.22 (m, 2H), 7.14 (dt, J=0.7, 7.4 Hz, 1H), 3.67 (s, 3H). m/z (ESI) 476.2 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by chromatography on silica gel (12-g Redi-Sep Gold column, 0-5% MeOH/DCM)

Sources & evidence

ORD record
ord-ac64597e38d14545bed3b48d015b1c8f
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

Loading…